ANNUAL & UPCOMING EVENTS in Middlebury
All year long, Middlebury is home to great events planned by local businesses and organizations, many of which are free or low-cost. Outdoor concerts, markets, parades, holidays festivities, a food truck festival…these are all events you can experience for yourself right here in Middlebury every year. Check them out!
Spring/Summer
BMP Midd Summer Markets
A downtown market series featuring live music and local artisans as well as delicious to-go food
Addison County Farmers Market
Join in every Wednesday June – Oct from 1:30 PM to 6:00 PM on the Middlebury Town Green for the Addison County Farmers Market — a weekly celebration of community, connection, and the incredible bounty of Vermont’s farms and food producers. 1 Merchant’s Row.
Memorial Day Parade
Hosted by the American Legion
Circus Smirkus
The Big Top Tour of Circus Smirkus is coming to Middlebury! July 5-6, 2025
Foodaroo
Food truck festival featuring live entertainment hosted by Middlebury Underground
Festival on the Green
A week-long free concert series on the town green
St Stephen’s Peasant Market
The area’s largest flea market and rummage sale
Lion’s Club Auction
Auction and BBQ on the green
Middlebury New Filmmakers Festival
A four-day event celebrating new filmmakers
Fall
Middlebury Car Show and Fall Festival
An event co-hosted by the BMP and the Addison County Chamber of Commerce
Middlebury Maple Run
Vermont’s Sweetest Half Marathon, 10K & 5k run
Kelly Brush Ride
Annual cycling fundraiser for the Kelly Brush Foundation, supporting adaptive sports
ACORN Tour de Farms
Casual cycling tour of Addison County farms
Middlebury Pride
Inclusive and family-friendly parade down Main St, followed by a festival in the green
Fall Family Market
An enthusiastic welcome to Middlebury College families, highlighting all there is to love about Middlebury!
Spooktacular
Trick-or-Treating down Main Street
Winter
Very Merry Middlebury
A month-long celebration of the holidays, including Midd Night Strolls with extended evening shopping, tasting and strolling
First Fridays
Evening shopping and dining downtown with dozens of participating businesses with doors open late, special deals, and good times to be had!
Follow Better Middlebury Partnership on Facebook and @experiencemiddlebury on Instagram for our most up-to-date information on local events not to miss!